Amixetrine

Last updated
Amixetrine
Amixetrine.png
Clinical data
Routes of
administration 		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-[2-(3-methylbutoxy)-2-phenylethyl]pyrrolidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H27NO
Molar mass 261.409 g·mol−1
3D model (JSmol)
  • O(CCC(C)C)C(c1ccccc1)CN2CCCC2
  • InChI=1S/C17H27NO/c1-15(2)10-13-19-17(14-18-11-6-7-12-18)16-8-4-3-5-9-16/h3-5,8-9,15,17H,6-7,10-14H2,1-2H3 Yes check.svgY
  • Key:ISRODTBNJUAWEJ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Amixetrine (INN; brand name Somagest; developmental code CERM-898) is a drug that was formerly marketed in France but is now no longer sold. [1] [2] According to various sources it has been said to be an anti-inflammatory, antidepressant, antispasmodic, anticholinergic, antihistamine, and antiserotonergic, but its definitive indications and pharmacology are unclear. [1] [2] The drug was first synthesized in 1969 and was introduced in France in 1972. [1] [2]

Synthesis

The treatment of isoamyl alcohol (1) with styrene (2) at -10 °C with dropwise addition of tert-butyl hypobromite gives (2-bromo-1-(isopentyloxy)ethyl)benzene (3). [3] [4] Displacement of the halogen leaving group by pyrrolidine completes the synthesis of amixetrine (4).

Synthesis of amixetrine Amixetrine synthesis.svg
Synthesis of amixetrine

References

  1. 1 2 3 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 80–. ISBN   978-1-4757-2085-3.
  2. 1 2 3 William Andrew Publishing (22 October 2013). "Amixetrine Hydrochloride". Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 285–. ISBN   978-0-8155-1856-3.
  3. ↑ GB 1253818 idem Mauvernay Roland Yves, Norbert Busch, DE1811767A1 (1969 to Ct Europ De Rech S Mauvernay)
  4. ↑ "-Butyl Hypobromite". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. 2009. doi:10.1002/047084289X.rb387.pub2. ISBN   978-0-470-84289-8.
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